1. Chapter 7 - Stereochemistry Enantiomers of bromochlorofluoromethane Non-superimposable mirror images – Enantiomers

2. Figure 7.1YSU

3. 7.12 Optically active molecules of biological importanceYSU

4. $100 billion sales worldwide in 2000 Account for 32% of the $360 billion total drug salesYSU

5. 7.2 The Chirality Center Carbon atom is asymmetric C is a stereogenic center Enantiomers are stereoisomers since the atoms at the stereogenic carbon are arranged differently in space.YSU

6. Mirror images of chlorodifluoromethane are superimposable Figure 7.2 Achiral i.e. not chiral 7.3 Symmetry in achiral structuresYSU

7. 7.4 Optical activity Figure 7.4 Typical polarimeter setup : [  ] D = 100 x (rotation)/(cell length) x (concentration)YSU

8. 7.8 Enantiomers same physical properties except rotation of plane polarized light one enantiomer positive rotation (+) other negative rotation (-)YSU

9. Which molecules contain chiral (stereogenic) centers? The stereogenic C must have 4 different groups attachedYSU

10. 7.5 Absolute and Relative Configuration Absolute Configuration – Actual arrangement of substituents in space (+)-2-butanol and (-)-2-butanol, but which is which? Relative Configuration - Configuration relative to another compound. Pre-1951, compounds could be related to each other but the absolute configuration was not able to be determined.YSU

11. 7.6 Nomenclature - Use of the Cahn-Ingold-Prelog System R enantiomerS enantiomer R - Rectus - the clockwise arrangement of groups S - Sinestre - the counterclockwise arrangement of groupsYSU (R) and (S)

12. 7.6 Nomenclature - Use of the Cahn-Ingold-Prelog SystemYSU

13. 7.7 Fischer projection formulas Figure 7.5 YSU

14. 7.9 Reactions that create a Chirality Center Figure 7.6 YSU

15. 7.10 Chiral molecules with two Chirality Centers Figure 7.7 YSU

16. 7.10 Representations of (2R, 3R)-dihydroxybutanoic acid All the same molecule: (a) and (b) differ only by bond rotation ; (b) leads to correct Fischer projection Conversion of “zig-zag” picture to Fischer projection Figure 7.8YSU

17. 7.10 Chiral molecules with two Chirality CentersYSU

18. 7.11 Achiral molecules with two Chirality Centers Figure 7.9YSU

19. Meso-2,3-butanediol Figure 7.10 YSU

20. 7.12 Stereogenic centers in cholic acid Figure 7.11YSU

21. 7.12 Optically active molecules of biological importanceYSU

22. 7.13 Reactions that produce diastereomers Figure 7.12YSU

23. 7.13 Reactions that produce diastereomers Figure 7.12YSU

24. 7.14 Resolution of a chiral substance into its enantiomers Figure 7.13YSU

25. Not covering 7.15 and 7.16 YSU